


Last Night in the Devildom

by TidalWaveKitty



Category: Shall We Date?: Obey Me!
Genre: Anal Fingering, Anal Sex, Double Anal Penetration, Everyone Is Gay, F/M, Gay, Gay Sex, M/M, MC is a slut and its fine, Male MC, Multi, Other Additional Tags to Be Added, Polyamory, Porn With Plot, Spitroasting, Threesome - M/M/M, bottom MC, but not a lot of plot?, chapter 20 spoilers, seven boys in one night
Language: English
Status: In-Progress
Published: 2020-03-05
Updated: 2020-03-05
Packaged: 2021-02-23 02:17:26
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,906
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23004166
Author URL: https://archiveofourown.org/users/TidalWaveKitty/pseuds/TidalWaveKitty
Summary: MC's last night in the Devildom, and Lucifer already has plans, but those other brothers are expecting me back. Trouble is sure to ensue.Writen with my own MC in mind.Looking for beta readers before chapters come out!
Relationships: Asmodeus (Shall We Date?: Obey Me!)/Original Character(s), Asmodeus/Main Character (Shall We Date?: Obey Me!), Beelzebub & Belphegor & Main Character (Shall We Date?: Obey Me!), Beelzebub (Shall We Date?: Obey Me!)/Original Character(s), Beelzebub/Main Character (Shall We Date?: Obey Me!), Belphegor (Shall We Date?: Obey Me!)/Original Character(s), Leviathan (Shall We Date?: Obey Me!)/Original Character(s), Leviathan/Main Character (Shall We Date?: Obey Me!), Lucifer (Shall We Date?: Obey Me!)/Original Character(s), Lucifer/Main Character (Shall We Date?: Obey Me!), Main Character/Mammon (Shall We Date?: Obey Me!), Main Character/Satan (Shall We Date?: Obey Me!), Mammon (Shall We Date?: Obey Me!)/Original Character(s), Satan (Shall We Date?: Obey Me!)/Original Character(s)
Comments: 2
Kudos: 65





	Last Night in the Devildom

**Notes for the Chapter:**

> A.N. Oof, heyo everyone! Jesus fuck, I’ve been reading Shall We Date games since forever, and I fucking screamed when this game came out. It’s obviously very different from their games in the past, but I love all of these boys so fucking much. I’ve always kinda disliked how the SWD games have always hinted at sexual endeavors, but they stopped writing them after..Mononoke Kiss and Ninja Love, you know? I don’t know what order these games came out and I’m so fucking sad that they are getting TERMINATED, like wow! Why?! Not important right now.  
> I’m writing this in first person, from my MC’s perspective, Chase! I hope you all like it, even if it isn’t specifically a reader insert!  
> WARNING: Spoilers for Chapter 20 in the game, when Lucifer oh so clearly states that he is fucking bedding you the night before you leave so, I wanted to expand on that! Because those boys expect you to come back to the party! And additional warnings for yaoi. Lots of it. Please enjoy!  
> And also, I know that the first part is purely taken from what happens in the app, I thought it was important to include it!

I had really only headed out to get a drink of water. That was all it was supposed to be, but the music had drawn me in so easily. In all the hussle and bussle of the last minute party upstairs, it wasn’t hard to realize that Lucifer hadn’t come to join the festivities. Which was definitely like him. 

When I stepped into the library, I could see that the secret study was cracked open, where the soft music was pouring out of. Again, not really a surprise for Lucifer. I stepped up to the door, ready to walk in on my own before hearing Lucifer’s voice call out.

“The door’s open.”

True to his words, it was. I pushed it open enough to walk inside the study, looking over to the raven. He was seated in one of the chairs in front of the fireplace, the embers casting a warm orange glow across his backside.

“It sounds like quite the party up in the attic. And thanks to the fact that everyone else is busy up there, I get to stay here and enjoy my music in peace,” he said rather smoothly, reddish gray eyes trained on my form, smile content for once.

“What is this you’re listening to?” I asked, because it sounded familiar.

“It’s nice, don’t you think? This is the cursed vinyl edition of  _ The Tale of the Seven Lords _ soundtrack, which you managed to borrow from Levi for me.” He shifted his legs, crossing them calmly as I stepped closer, resting my hands against the back of the other chair.

“Don’t people say that you’ll die if you listen to it?”

“That’s right. I see you haven’t forgotten the story behind it. Still...it’s true that all humans involved in its creation died mysteriously, but that was nothing more than coincidence. And even if this soundtrack really were cursed, look who you’ve got by your side right now. You’re standing here chatting with one of the most powerful demons in the Devildom. So you don’t have anything to worry about, now do you?” He gave a small, dismissive wave with his gloved hand, more of a mocking smile on his lips.

But the smile dropped after a moment and he glanced to the side, over to the desk. “It was in this very room that I selected you for our exchange program. When I first welcomed you here, I was only doing it for Diavolo. I figured that if you managed to survive a year here without any incidents, that was really all I could ask for. And even if things didn’t go as planned, as long as I could keep you from getting eaten by any of the lower-level demons, everything would be all right. That’s what I thought…” His eyes returned to my face, smiling again, but only for a moment. “But I somehow managed to choose a human who’s such a magnet for trouble that it almost defies belief, wouldn’t you say? There were times when I thought that I’d made a mistake by choosing you.”

“How about now?” I asked, tilting my head. I had to say, I felt a little guilty in the beginning for causing a big fuss, but everything seemed better now, didn’t it?

“What do you think? I’d say you know the answer. I made the right choice in selecting you for the program. You’ve kept me quite entertained over the past year. In fact, it’s probably the  _ most _ entertained I’ve been in my whole life.” There was that content smile again. 

I couldn’t help but think back on all the times Lucifer had called me out, saying I was acting out of line. Then saying I was special, changing them. 

I thought of Lilith. The sight of Lucifer clutching her so tightly still made my chest tighten. 

Lucifer’s voice broke me from my thoughts. “So then, Chase...have you done all you set out to do here in the Devildom? No unfinished business? No loose ends?” 

I blinked before looking at him with a soft smile. “I still haven’t made a pact with you.” Sure, that wasn’t the original goal of getting through this year, but..it seemed strange, having only six out of seven. An incomplete set. Incomplete, because Lucifer needed to be there too. Things wouldn’t be the same without him. 

“A pact, you say? I see. You’ve made pacts with all of my brothers, which just leaves me.” He stood up from his chair slowly. “Do you really want to make a pact with me? Truly? I don’t know how my brothers felt about making a pact with you, but I am more than a name to be crossed off of your list.” His stance was rigid. The hairs at the back of my neck started prickling. This messed with his pride, didn’t it?

“I can’t have you lumping me together with everyone else. That won’t do.” Darkness engulfed him, and I knew that when it cleared, Lucifer would be in his true form. I withdrew my hands from the chair, standing a little straighter. But when Lucifer stepped around the chair to confront me, I didn’t run, looking up at his face calmly.

“You aren’t going to run? You’ve certainly got guts, don’t you? I’ve always found that aspect of you irritating.” His red, gloved hand raised up before resting against my chin, tipping my head back more. “But as irritating as it is, it’s even  **more** endearing.” Lucifer quickly dropped his hand, tipping his head back, but more in that usual way so he could glare down at me.

“Now listen, and listen well. I will not be your possession. I won’t belong to you.  **You will belong to me.** So, what will it be? Will you make a pact with me, Chase?” He stretched his hand out again.

“Yes, I’ll make a pact with you.” My hand easily reached out to shake his, liking the smooth leather feel against my palm.

“...Good. Then it’s done. As of this moment, Chase, you are  **mine** .” 

Set complete. It felt good. It felt whole, and it easily brought a smile to my face.

“I assume that takes care of all your loose ends?” He asked, releasing my hand.

Gently shaking my head, my smile only grew brighter. “There’s still something I have to do.”

Lucifer looked a little amused by the thought. “There is?”

My hands were a little more shaky than with the other boys. Things would be fine though. Lucifer said I was his, that had to mean something. I reached out to grasp his cheeks gently, pulling him down as I went up on my tip toes, pressing my lips to his. The sensation was brief, Lucifer easily pulling back from my hold. 

“...Chase. I’ve always known that you wanted to do this.”

I tensed a little at being called out, once again. Always? Always wasn’t really that long ago. Kissing Lucifer was definitely newer on the list.

“And I know what you’d like to do next as well. We’re heading straight to my room. You’re going to spend your last night in the devildom there, together with me,” his arms were around me quickly, hands dipping into the space between the backs of my thighs to hoist me up, “...all night long, until the break of dawn. I’m not letting anyone else have you now... **You’re mine.** ”

That thought was very tempting, and I didn’t hesitate to wrap my legs around his waist, face flushing. Spending the night with Lucifer sounded so very heavenly, but also a little bit worrisome. Still, Lucifer easily walked out of the study, leaving behind the soft music. 

When Lucifer finally let me go, I dropped back onto the red satin sheets that I knew belonged to his bed. I must have been distracted by his hands groping at my rear for most of the walk, because I hadn’t even realized that he had changed back to his more human-like form. I was almost disappointed, but I felt like asking would just lead to further complications. Tonight wasn’t the time for that. He must have shut the door as soon as we came through it, because he was already stripping, coat dropped onto the floor behind him.

“Chase, strip. Completely bare. I don’t want anything in my way.” His commanding tone sent a jolt of excitement straight to my groin. I quickly moved to sit up, shifting about haphazardly to push off my pants and boxers before removing my sweater vest, tossing it aside as my fingers started to fumble with the buttons of my shirt. 

I was only half way down when I felt fingers in my hair, forcing my head back to look up at Lucifer. He must have been much better with buttons, because his shirt was already gone, slacks undone and drooping on his hips, and  _ holy crap _ . My mouth went a little dry at the sight of Lucifer’s half hard cock already trying to stand up. 

“Suck it,” he demanded, eyes shining with a little more redness.

I swallowed the lump in my throat before reaching my hands out to grasp at his member, parting my lips and leaning forward to let my mouth envelop the tip of his shaft. It was hot, and filled my mouth easily. Fantasizing about doing this was a hell of a lot easier than actually doing it. I let my tongue swirl around the tip, sloppy, drool easily escaping my mouth. Lucifer’s fingers tightened in my hair before pulling me closer, forcing himself further into my mouth.

I had no idea what I was really doing, feeling my top teeth awkwardly scrap against his member, shifting my tongue to try and stop the lower half from suffering the same fate. He was getting harder in my mouth, and I felt confident enough to pull my hands away to continue unbuttoning my shirt blindly. My eyes slipped shut, moving my lip carefully to try and help aid in preventing my teeth from hitting too much.

I heard the quietest of groans from above me as Lucifer continued to tug at my hair, guiding me through sucking him off. I could feel his length nearly reaching the back of my throat. Lucifer pulled back, the stinging sensation easing. But I could also feel that even with how much he was shoving in my mouth, it was nowhere near his whole girth. My thighs quivered a little bit at the thought. 

I wasn’t sure just how long he was slowly fucking into my mouth, but he pulled back, and I heard fabric russling before dropping to the floor and when I opened my eyes, I wasn’t very shocked to find him completely bare. I quickly slid my shirt off my shoulders before tossing it aside as well. When Lucifer finally let go of my hair, he stepped back. 

“Get comfortable on the bed. Backside up. I’m gonna stretch you until you’re begging for it.” He calmly stepped around his bed to the nightstand, pulling open a drawer. 

I didn’t hesitate to follow his orders, moving up to the pillows, laying on my stomach before pushing my hips up into the air, heart beating wildly in my chest. 

The bed shifted beside me and I heard a soft pop before suddenly a cool, slick finger rubbed over my entrance, the sensation bringing a gasp to my lips. Lucifer didn’t hesitate to slide the digit inside before I felt more slickness dripping onto my backside. The sensation was strange, but definitely wanted. Feeling his finger sliding over my walls only made my heart go even more wild. He easily slid in a second finger, a soft moan leaving my throat. The bed shifted again and Lucifer twisted his wrist a little bit. 

His fingers dragged over a new spot, and my back arched, a louder moan leaving this time and I felt Lucifer’s other hand grabbing hold of my left cheek. “There it is. That weak spot of yours. What shall we do with it?” He asked, leaning to loom over me more.

“Ah, Lucifer...please,” I muttered, slowly turning my head to try and look back at him. 

“Mm, just saying please don’t really sound like begging, Chase.” His fingers moved to scissor apart, deliberately avoiding the spot.

Whining softly, chest pressing further into the bedding, I pushed my hips backwards into his hand. “Please Lucifer, touch me again. I want you to touch that spot more.”

I could hear him hum before finally feeling his fingertips pressing into my prostate, rubbing over it. “I suppose that will do for now.”

I knew that my voice was getting louder the longer things went on. Lucifer eventually slid in a third finger, alternating his movements between scissoring me open, thrusting, and rubbing over my prostate like it was a button. Everything felt slick at my rear, excess lube easily dripping down my taint and my balls. I couldn't complain though, because all that lube left me feeling completely comfortable. My cock was aching, I needed more.

Rolling my shoulders, I pushed back roughly into his hand. I already knew what he wanted, he’d asked for it. “Lucifer. Fuck me, please. I need you inside me. Need your cock filling me.” The flush on my face renewed, but it was well worth it, feeling Lucifer falter in his movements.

There came a breathy laugh as Lucifer withdrew his fingers. “You always did seem a little needy.” The bed shifted again, Lucifer’s legs sliding between mine, knees pressing together.

It felt like I was trying to compete with Asmo for the title of Avatar of Lust with the way I was pushing my hips back again to try and find Lucifer’s. His hands moved to hold my waist, rolling his hips forward to let his shaft run between the cleft of my rear. He repeated this a few times before the tip caught against the rim, pushing in slowly, agonizingly calm.

Definitely thicker than his fingers, it stretched me more, but the wetness aided in making the stretch less painful. When I felt Lucifer’s hips pressed against my own, I moaned, fingers tightening into one of the pillows, pulling it under myself. It helped put a little less stress on my back. 

His pace was slow at first, pushing one of his hands up the curve of my spine before raking his nails back down. He did this a few times, probably leaving soft red marks in his wake before Lucifer grabbed my hips forcefully, quickening his pace. 

Moans turned to mewls, mixing with the sound of skin slapping together, filling his room. One of Lucifer’s hands slid over my side, running over my stomach before taking hold of my shaft. 

Lucifer leaned over more as he started pumping his hand. “You’re getting tighter, Chase. Why don’t you keep begging for what you want?” His voice was a low rumble next to my ear, sending shivers down my spine.

“Lu..Lucifer...fuck me, harder. I wanna cum...” I managed out between the moans, hips desperately trying to buck into both sensations that were driving my senses crazy with how good they felt.

“Good boy. Because it’s your last night, I’ll go easy on you.” His steady fast pace quickly turned more to quick snaps of his hips, ramming deeper and harder with every thrust.

I clenched my eyes shut, nails digging into the fabric before it all became too much.

“LUCIFEEER!” With a loud cry of his name, I quickly came undone feeling a little guilty for getting his sheets messy, but feeling too good to really apologize for it. Lucifer continued moving for a few seconds more before a low groan, lips attaching onto my ear before feeling a new wetness inside.

My thighs trembled as I tried to catch my breath, turning my head a little to try and rest more comfortably before Lucifer pulled back from my ear, leaning back straight again. His hand moved from my hip to grab my cheek, pulling it aside, thumb stretching my rim a little bit.

“To think, a human like you could satisfy me so easily.” There was a beat before he moved to pull out completely, gently pushing my hips down to the bed. “Rest for a bit.”

I could feel the mess under my stomach, but I just nodded, heartbeat still rapidly pounding in my ears. Lucifer was shifting on the bed before there came a rumble from the hallway, and it stopped just outside the door. There was a moment before the handle jiggled and the door bursts open. 

Mammon, first in line of the group, stood in the doorway, hand still clutching tightly onto the doorknob as he looked on at us. Shock crossed his face before it seemed to be replaced with anger. “Lucifer, you scummy jerk! I should have known nothing good was happening in here!” He stepped away from the door, darkness enveloping him the closer he got.

The five other boys remained poised by the doors, glancing between me and Mammon’s approaching figure.

Lucifer sighed as he stood up, facing Mammon head on as he emerged in his demon form, wings fretting behind his back anxiously. It was a little amusing to see Lucifer standing there completely naked, but unashamed. “You guys were off doing your own thing. You’re always butting in like you think you have some kind of authority. Chase isn’t just yours.”

Mammon’s cheeks heated up as he glared daggers at his older brother. “It ain’t because of that! What do you expect us to do when we hear him yelling so loudly? Anyone would assume that something bad was happening!”

I turned my face into the pillow a little more. Had my voice really carried that much? No way.

Belphegor stepped forward. “Chase said he was getting a drink. When he didn’t come back, we all got worried about where he went. We just so happened to hear him when we came downstairs, that was all. Of course we were gonna come check.”

Satan clicked his tongue as he crossed his arms over his chest. “You haven’t really had the best track record with Chase, Lucifer. You were the one that kept getting mad at him.”

Lucifer sighed and reached up to rub over his temple in annoyance. “Fine, whatever. But you found out what was happening, problem solved. Now, get out.”

“No way! You can’t just keep Chase to yourself!” Mammon started, “He was hanging out with  _ all _ of us tonight!”

“Chase didn’t even get to have his turn playing the game,” Levi muttered, not really looking, like he was the only one embarrassed about the situation.

Asmo was the one that perked up and butted through the crowd, raising his hand like an eager child in class. “Oh, oh! If you get to spend the night with Chase in bed, I want to, too!”

There was a pause of silence between all of the boys before Lucifer glanced back to me. I couldn’t help thinking about it, about all of them...doing what Lucifer had done. It certainly wasn’t the first time imagining it, but it still brought a flush to my face as I avoided his gaze.

Lucifer moved back to the bed, patting my lower back. “It is Chase’s choice, but if  _ all _ of you were willing to share...” His fingertips trailed down to my rear, bringing out a squeak. “I can already tell the thought doesn’t bother him.”

I turned my gaze slowly, looking at Mammon. His face was still red, but I could see the way he nibbled at his bottom lip, like he was genuinely thinking about it.

“I’d share!” Asmo squealed, pushing past Mammon and leaping onto the bed beside me. “You want to, don’t you Chase?”

I looked over each of the boys before slowly pushing myself to sit up, biting my cheek before nodding. “I...I’d like to.”

He squealed, wrapping me up in a hug and nuzzling into my cheek before Lucifer pulled him back by his scarf. “You’ll have to have patience, Asmo. I think it’s only fair to go from oldest to youngest. So that Mammon can get that selfishness out of the way. Wouldn’t you say so?” He looked over to the white haired male.

Mammon was still looking conflicted about it, huffing and opening his mouth like he wanted to say something, only to shut it and turn away, stomping out of the room.

Asmo whined, but pulled himself off the bed. “I suppose. Mammon would just bug everyone else until he got a turn anyways. I’ll wait. Ah, I’ll make sure everything is ready in my room, then!” And with that, he was rushing out of Lucifer’s bedroom.

“Why don’t the rest of you boys do the same thing?” Lucifer offered. 

Belphegor stood silently for a moment before quickly turning, latching onto Beel’s arm and dragging him off to what I could only assume was their shared room. I couldn’t help but think about Belphie’s offer. Him and Beel.  _ Both _ of them. I swallowed a little thickly before slowly trying to move off the bed.

Satan shook his head, shrugging his shoulders. “I suppose. Though, I figured that you of all people would understand why this was a bad idea, Lucifer.” He turned and stepped out the door. Satan had already said he wanted more, but there hadn’t been time— and that had been yesterday.

With the other five gone, Levi stood in the doorway awkwardly, glancing up at me before turning away. “As if a normie would ever wanna do something like that with me!” Levi was probably still telling himself that earlier today was an accident. It was almost cute to see him retreating. 

I glanced at Lucifer as I sat on the edge of the bed. “Was that...really okay?” I asked softly.

He shook his head as he stood up and started picking up his clothes. “No, but I know that none of them would have shut up about it. This was the simpler way of taking care of them. I wish that they had just stayed upstairs.” He folded everything neatly before he glanced back at me. “You know Mammon well enough to know how he’ll be. That greed of his doesn’t just lie with money. He might never say it, but he’s greedy with you too. Then again, most of those boys are now. You really are something special, Chase.”

I smiled as I carefully stood up, stretching my limbs before moving for my discarded clothes.

“Just take your underwear,” Lucifer stated, taking my shirt from me. “You really won’t need anything else for tonight.”

My face flushed a fresh shade of pink before nodding, pulling my boxers on. Before leaving, I didn’t hesitate to latch my hands onto Lucifer’s cheeks again, trying to drag him into another kiss. Though considering his strength, I knew he was the one that was really accepting the kiss. “Keep that up and I really won’t be able to let you go,” he said, pulling his face back as he tossed my pants over his forearm.

I already knew that everyone was waiting for me, and imagining Mammon, I didn’t want him to be sulking, so I gave a wave goodbye, shutting Lucifer’s door behind me.

**Notes for the Chapter:**

> I'm still looking for a few more beta readers to help with sentence structure and grammar! If you're interested, go ahead and add me on discord, TidalWaveKitty#1763 and just tell me you wanna beta! If you don't have discord, leave a comment and we can figure something else out!   
> Thanks for reading!


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